Questions to ask your crush
These are built for a text thread, not a table — short enough to send, open enough to answer with more than one word, and none of them make it obvious that you have been thinking about what to send.
Easy ones, to start
Nobody opens with the hard question. These are the ones you can ask with the plates still on the table, and they still tell you something.
- Who's in your corner without you ever having to ask them to be?
- Who in your life is impossible to be in a bad mood around?
- What's an achievement of yours that sounds completely unimpressive out loud?
- Who did something small for you recently that landed much bigger than they'd have guessed?
- Who's the last person you thanked properly, and what was it for?
- What's the nicest message anyone has ever sent you?
- What kind of tired are you today?
- What do you do when you can't sleep?
- What's your reply when someone asks how you are and you don't want to get into it?
- When you walk into a room full of strangers, what do you clock first?
- What's the first thing you do when you get in, before you've even taken your coat off?
- What's a book, film or show that changed something in you, and what did it change?
- What were you listening to at fifteen that you'd still defend now?
- What are you a bit of a snob about, and when did that start?
- What's a strong opinion you hold about something that doesn't matter at all?
- What's a phrase you say so often your friends could do an impression of you?
Questions that actually go somewhere
The middle rung. Still safe, but the answer is about who someone is rather than what they did, which is the whole difference.
- What actually changes in you when you like someone? Genuinely.
- What's the fastest way for someone to lose your interest?
- What are you scared of being seen as?
- What do you want people to notice about you that they usually miss?
- What would someone have to notice about you for you to think, right, they get it?
- When you don't want to answer something, what's your move?
- Who do you turn into around your family?
- What has to happen before you feel properly comfortable around someone?
- Which of your friendships would tell someone the most about you, and what would it tell them?
- What are you better at than you're comfortable claiming?
When something is off
The ones people skip. Skipping them is usually why the same thing keeps coming back.
- Are you someone who says the awkward thing, or waits for it to pass?
- What's the fastest way to irritate you that has nothing to do with anything important?
- If two people in a group start bickering, what do you end up doing?
- How long can a message sit there before you start feeling bad about it?
- What do you do when you can't tell if someone likes you back?
- What's something you've been meaning to ask me and haven't?
- How do you let someone know you're interested, and has it ever gone wrong?
- What's a mixed signal you've sent before, without meaning to?
Where things are going
Fewer of these on purpose. A conversation that is only about the future is a planning meeting.
- What's a habit you picked up this year that you'd be annoyed to lose?
- What are you trying to get better at at the moment?
- What have you booked or agreed to that you'd be gutted to miss?
- What's the daydream you've had running for years?
- What's something you've wanted for years that you don't say out loud much?
- What are you looking forward to about being older, and what are you not?
- What would you want to have got properly good at by the time you're fifty?
- What did you believe about yourself at school that you've had to unlearn?
Some questions are easier to answer when neither of you chose them.
Turn one over. You would not have picked it — that is the point.
Six questions from this page, face down.
On the site they live on a wheel. You spin, it lands, nobody chose it.
Does any of this actually work?
The uncomfortable finding first: text is the medium people choose and the one that underperforms. In a field experiment, people asked to reconnect with an old friend by phone rather than email felt more connected afterwards than those assigned email. In the lab, strangers paired over video, voice or voice-chat formed stronger bonds than those paired over text — and, critically, with no increase in awkwardness. People predicted the voice conditions would be more uncomfortable. They were not. The preference for text is built on an expectation that the data does not support.
So the honest job of a question sent over text is to get to a call, not to substitute for one. That is a smaller claim than this genre usually makes, and it is the one the evidence carries.
The other thing worth knowing is that you cannot screen for this in advance. Two speed-dating studies had participants complete more than 100 self-report measures of traits and preferences before meeting anyone. Machine-learning models predicted 4–18% of how much a person wanted others in general and 7–27% of how much they were wanted — and none at all of whether two specific people would want each other. Every hour spent working out whether they are right for you before you have actually talked is spent on the one quantity that turned out to be unpredictable.
Kumar & Epley (2021), It’s surprisingly nice to hear you: Misunderstanding the impact of communication media can lead to suboptimal choices of how to connect with others, Journal of Experimental Psychology: General · source
Joel, Eastwick & Finkel (2017), Is Romantic Desire Predictable? Machine Learning Applied to Initial Romantic Attraction, Psychological Science · source
No question makes someone interested who isn't. What these do is give a conversation somewhere to go on a night when it would otherwise die at "haha same" — which is a smaller claim than the search results on this topic will make you.
Last checked 28 August 2026.